Trichostatin A
Basic information
- CAS
58880-19-6- Standard SMILES
CC(/C=C/C(=O)NO)=C\[C@@H](C)C(=O)c1ccc(N(C)C)cc1- InChIKey
RTKIYFITIVXBLE-QEQCGCAPSA-N- Molecular formula
- C17H22N2O3
- Average molar mass
- 302.37 g/mol
- Monoisotopic mass
- 302.16304257
Overview
Trichostatin A is a hydroxamic acid, a trichostatin and an antibiotic antifungal agent. It has a role as a geroprotector, an EC 3.5.1.98 (histone deacetylase) inhibitor and a bacterial metabolite. It is functionally related to a (R)-trichostatic acid.
Names & identifiers
- Preferred name
- Trichostatin A
- IUPAC
- (2E,4E,6R)-7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide
- English name
- TRICHOSTATIN A
- Molecular formula
- C17H22N2O3
- Molecular weight
- 302.37
Names & synonyms
trichostatin A58880-19-6TSA antibioitcDTXSID6037063CHEBI:460243X2S926L3Z2,4-Heptadienamide, 7-(4-(dimethylamino)phenyl)-N-hydroxy-4,6-dimethyl-7-oxo-7-(4-(Dimethylamino)phenyl)-N-hydroxy-4,6-dimethyl-7-oxo-2,4-heptadienamideVTR297VTR-297(2E,4E,6R)-7-(4-(dimethylamino)phenyl)-N-hydroxy-4,6-dimethyl-7-oxo-2,4-heptadienamideNSC-311042
Show more names
A 300ICS-210CS-2704richostatinA(R)-Trichostatin A(+)-Trichostatin ATrichostatin A (TSA)
7-[4-(DIMETHYLAMINO)PHENYL]-N-HYDROXY-4,6-DIMETHYL-7-OXO-2,4-HEPTADIENAMIDENSC311042RefChem:899268DTXCID4017063611-758-2(2E,4E)-7-(4-(dimethylamino)phenyl)-N-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamideTrichostatinTSA
Database identifiers
- CAS
58880-19-6
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 69.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 6
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 447
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LipidsPolyketides [PK] -> Linear polyketides [PK01]
Physicochemical properties
- Melting point
- 140 · 140-143℃
- alpha
- 20.5 · D20.5 +62.8° ±1.1° (c = 1.007 in ethanol)
- Density
- 1.139 · 1.139
- refractive index
- 136 ° · 136 ° (C=0.3, MeOH)
- storage temp.
- -20 °C · -20°C
- solubility
- 1 mg/mL · ethanol: 1 mg/mL
- form
- Off-white lyophilized solid
- pka
- 8.93 · 8.93±0.23(Predicted)
- color
- Tan
- biological source
- Streptomyces sp.
- Merck
- 14 · 14,9649
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302+H312+H332 (15%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 187 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (99.5%)
Safety data
- wgk
- 3
- rtecs
- MI5215000
- ridadr
- NA 1993 / PGIII
- hs_code
- 29280000
- risk_code
- 20/21/22-36/37/38-43
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302+H312+H332-H315-H317-H319-H335
- Precautionary statements
- P261-P280-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins.
Compounds that inhibit HISTONE DEACETYLASES. This class of drugs may influence gene expression by increasing the level of acetylated HISTONES in specific CHROMATIN domains.
Applications
DescriptionTrichostatin A (58880-19-6) is a potent and selective histone deacetylase (HDAC) inhibitor (Ki = 3.4 nM). Induces reversion of ras transformed cells to normal morphology. Trichostatin A induces dedifferentiation of primordial germ cells into embryonic germ cells. Cell permeable and active in vivo.
UsesTrichostatin A is a histone deacetylase inhibitor that enhances the cytotoxic efficacy of anticancer drugs that target DNA. Trichostatin A displays antifungal, antiprotozoan and antitumour activity
UsesTrichostatin A, ready-made solution has been used:as a histone deacetylase inhibitor to study its effect on transcriptome changes by stem cell testingto inhibit histone deacetylase (HDAC) class I, II, or III in primary pituitary cell cultures and to investigate insulin control of endogenous human growth hormone gene (hGH)to treat cells for the HDAC inhibition experiments
UsesTrichostatin A is a known inhibitor of fibrosis in vitro and in vivo, and is used as an anticancer agent. Potent differentiation inducer of friend leukemic cells.
General DescriptionTrichostatin A is a compound of primary hydroxamic acid.
Additional notes
Related reactions
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Compound notes
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